Bis(L proline) hydrogen nitrate

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organic papers

o862

S. Pandiarajanet al. 2C₅H₉NO₂H+NO₃ÿ DOI: 10.1107/S1600536802012394 Acta Cryst.(2002). E58, o862±o864 Acta Crystallographica Section E

Structure Reports

Online ISSN 1600-5368

Bis(

L

-proline) hydrogen nitrate

S. Pandiarajan,a_{B. Sridhar}b_and

R. K. Rajaramb_*

a_{Department of Physics, Devanga Arts College,}

Aruppukottai 626 101, India, andb_Department

of Physics, Madurai Kamaraj University, Madurai 625 021, India

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study T= 293 K

Mean(C±C) = 0.005 AÊ Rfactor = 0.047 wRfactor = 0.121 Data-to-parameter ratio = 7.7

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

In the title compound, 2C5H9NO2H+NO3ÿ, the two proline

residues are linked by a strong OÐH O hydrogen bond, with an O O distance of 2.414 (3) AÊ. In one of the residues, the pyrrolidine ring adopts an envelope conformation, while in the other it adopts a half-chair conformation. NÐH O hydrogen bonds link the two residues to form double-chain structures down theaaxis, which are interlinked by NÐH O hydrogen bonds involving the O atoms of the nitrate ions.

Comment

In proline (2-pyrrolidinecarboxylate), the -amino group is not free but is substituted by a portion of itsRgroup to yield a cyclic structure; thus, this imino acid has a unique conforma-tion. Proline, with the help of vitamin C, is essential in the manufacture of collagen. It enhances skin texture and strengthens body joints, tendon and heart muscle. The crystal structures of l-proline monohydrate (Kayushina & Vainsh-tein, 1965; Verbist et al., 1972; Janczak & Luger, 1997), dl -proline hydrochloride (Mitsui et al., 1969), dl-homoproline tetrahydrate (Bhattacharjee & Chacko, 1979), dl-proline monohydrate (Padmanabhan et al., 1995) and bis(l-proline) hydrogen(1+) perchlorate (Pandiarajanet al., 2002) have been reported. In the present study, the crystal structure determ-ination ofl-proline reacted with nitric acid was undertaken to study the effect of the inorganic acid on the conformation of the proline molecule and the hydrogen-bonding scheme.

The asymmetric unit of (I) contains two crystallographically independent proline residues (AandB) and hydrogen nitrate. The conformation angles 1 _{for the proline residues are}

ÿ8.3 (4) andÿ10.0 (5)_{. The conformation angles}1_, 2_,3_,

4_and_{of the pyrrolidine ring for residues}_A_/_B_are_ÿ_{41.6 (3)/}

ÿ30.2 (4), 39.7 (3)/36.8 (5), ÿ23.9 (4)/ÿ27.7 (5), ÿ2.1 (3)/ 8.0 (5) and 27.0 (3)/14.3 (4)_{, respectively (Prasad & Vijayan,}

1993). The conformation of the pyrrolidine ring, in general, is intermediate between half-chair and envelope (Prasad & Vijayan, 1993; Padmanabhan et al., 1995). In the present structure, the pyrrolidine ring in residueAadopts an envelope conformation [q2= 0.411 (4) AÊ and'2= 249.7 (5)], while in

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residueBit adopts a half-chair conformation [q2= 0.342 (4) AÊ

and'2= 264.5 (6)] (Cremer & Pople, 1975; Nardelli, 1983).

The H atom liberated from the nitric acid links the two residues by a strong hydrogen bond [O2BÐH2B O1Bi

2.414 (3) AÊ; symmetry code: (i)xÿ1,y, z]. These pairs are also linked by strong NÐH O hydrogen bonds (N21Ð H21B O1B) to form an in®nite one-dimensional chain along thea direction. The symmetry-related chains are interlinked by three-centred NÐH O hydrogen bonds [N11Ð H11B O1Aiii _{and N11ÐH11}_B_O2_Aiv_{; symmetry codes:}

(iii)xÿ1/2, ÿyÿ1/2, 1ÿz; (iv) 1/2+x, ÿyÿ1/2, 1ÿz] to form double chains along thea axis. In the crystal, these double-chain structures are interlinked by NÐH O hydrogen bonds involving the nitrate O atoms. A zigzag (Z1) head-to-tail sequence involving residueAis observed. An intramolecular NÐH O hydrogen bond is present in residueB, as found in

l-proline monohydrate at 100 K (Janczak & Luger, 1997).

Experimental

The title compound, (I), was crystallized at room temperature by slow evaporation of an aqueous solution ofl-proline and nitric acid in a stoichiometric ratio of 2:1.

Crystal data

2C5H9NO2H+NO3ÿ

Mr= 293.28

Orthorhombic,P212121

a= 7.2006 (6) AÊ b= 7.711 (1) AÊ c= 24.060 (3) AÊ V= 1335.9 (3) AÊ3

Z= 4

Dx= 1.458 Mg mÿ3

Dm= 1.454 Mg mÿ3

Dmmeasured by ¯otation method in a mixture of carbon tetrachloride and xylene

MoKradiation Cell parameters from 25

re¯ections = 11.3±13.9 = 0.12 mmÿ1

T= 293 (2) K Block, colourless 0.50.50.5 mm

Data collection

Enraf±Nonis CAD-4 diffractometer !±2scans

Absorption correction: scan (Northet al., 1968) Tmin= 0.916,Tmax= 0.937

3718 measured re¯ections 1430 independent re¯ections 1276 re¯ections withI> 2(I)

Rint= 0.019

max= 25.5

h=ÿ1!8 k=ÿ1!9 l=ÿ29!29 3 standard re¯ections

frequency: 60 min intensity decay: none

Re®nement

Re®nement onF2

R[F2_{> 2}₍_F2_{)] = 0.047}

wR(F2_{) = 0.121}

S= 1.16 1430 re¯ections 186 parameters

H atoms treated by a mixture of independent and constrained re®nement

w= 1/[2₍_F

o2) + (0.0703P)2 + 0.319P]

whereP= (Fo2+ 2Fc2)/3 (/)max< 0.001

max= 0.32 e AÊÿ3

min=ÿ0.29 e AÊÿ3

Extinction correction:SHELXL97 Extinction coef®cient: 0.102 (9)

Table 1

Selected geometric parameters (AÊ,_).

O1AÐC11 1.216 (3)

O1BÐC11 1.250 (3) O2O2ABÐC21ÐC21 1.188 (4)1.282 (4)

O1AÐC11ÐC12ÐN11 ÿ8.3 (4)

C13ÐC12ÐN11ÐC15 27.0 (3)

N11ÐC12ÐC13ÐC14 ÿ41.6 (3)

C12ÐC13ÐC14ÐC15 39.7 (3)

C12ÐN11ÐC15ÐC14 ÿ2.1 (3) C13ÐC14ÐC15ÐN11 ÿ23.9 (4)

O2AÐC21ÐC22ÐN21 ÿ10.0 (5)

C23ÐC22ÐN21ÐC25 14.3 (4)

N21ÐC22ÐC23ÐC24 ÿ30.2 (4)

C22ÐC23ÐC24ÐC25 36.8 (5)

C23ÐC24ÐC25ÐN21 ÿ27.7 (5)

C22ÐN21ÐC25ÐC24 8.0 (5)

Table 2

Hydrogen-bonding geometry (AÊ,_).

DÐH A DÐH H A D A DÐH A

O2BÐH2B O1Bi _{1.11 (6)} _{1.40 (6)} _{2.414 (3)} _{148 (5)}

N11ÐH11A O1ii _0.90 _2.30 _{3.045 (4)} ₁₄₁

N11ÐH11A O3ii _0.90 _2.42 _{3.231 (6)} ₁₅₁

N11ÐH11B O1Aiii _0.90 _2.12 _{2.825 (3)} ₁₃₅

N11ÐH11B O2Aiv _0.90 _2.25 _{2.932 (3)} ₁₃₂

N21ÐH21B O2A 0.90 2.22 2.676 (3) 111

N21ÐH21B O1B 0.90 2.14 2.792 (3) 128

N21ÐH21A O2 0.90 2.01 2.879 (5) 161

N21ÐH21A O1 0.90 2.39 2.982 (4) 124

Symmetry codes: (i) xÿ1;y;z; (ii) 1

2x;12ÿy;1ÿz; (iii) xÿ12;ÿ12ÿy;1ÿz; (iv) 1

2x;ÿ12ÿy;1ÿz.

The H atom linking the two proline residues was located and re®ned isotropically. All other H atoms were placed in geometrically calculated positions and included in the re®nement in a riding-model approximation, withUisoequal to 1.2Ueqof the carrier atom.

Data collection: CAD-4 Software (Enraf±Nonius, 1989); cell re®nement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure:SHELXL97 (Sheldrick, 1997);

Acta Cryst.(2002). E58, o862±o864 S. Pandiarajanet al. 2C₅H₉NO₂H+NO₃ÿ

o863

organic papers

Figure 1

The molecular structure of (I), showing the atomic numbering scheme and 50% probability displacement ellipsoids (Johnson, 1976).

Figure 2

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organic papers

o864

S. Pandiarajanet al. 2C₅H₉NO₂H+NO₃ÿ Acta Cryst.(2002). E58, o862±o864

molecular graphics:PLATON(Spek, 1999); software used to prepare material for publication:SHELXL97.

BS and RKR thank the Department of Science and Tech-nology (DST), Government of India, for ®nancial support. One of the authors (SPR) thanks the management of Devanga Arts College, Aruppukottai, India, for permitting him to pursue his doctoral research work.

References

Bhattacharjee, S. K. & Chacko, K. K. (1979).Acta Cryst.B35, 396±398. Cremer, D. & Pople, A. (1975).J. Am. Chem. Soc.97, 1354±1358.

Enraf±Nonius (1989).CAD-4Software. Version 5.0. Enraf±Nonius, Delft, The Netherlands.

Janczak, J. & Luger, P. (1997).Acta Cryst.C53, 1954±1956.

Johnson, C. K. (1976).ORTEPII. Oak Ridge National Laboratory, Tennessee, USA.

Kayushina, R. L. & Vainshtein, B. K. (1965).Kristallogra®ya,10, 833. Mitsui, Y., Tsuboi, M. & Iitaka, Y. (1969).Acta Cryst.B25, 2182±2192. Nardelli, M. (1983).Acta Cryst.C39, 1141±1142.

North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968).Acta Cryst.A24, 351± 359.

Padmanabhan, S., Suresh, S. & Vijayan, M. (1995).Acta Cryst.C51, 2098±2100. Pandiarajan, S., Sridhar, B. & Rajaram, R. K. (2002).Acta Cryst.E58, o74±o76. Prasad, G. S. & Vijayan, M. (1993).Acta Cryst.B49, 348±356.

Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of GoÈttingen, Germany.

Spek, A. L. (1999). PLATON for Windows. Utrecht University, The Netherlands.

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supporting information

sup-1 Acta Cryst. (2002). E58, o862–o864

supporting information

Acta Cryst. (2002). E58, o862–o864 [https://doi.org/10.1107/S1600536802012394]

Bis(

L

-proline) hydrogen nitrate

S. Pandiarajan, B. Sridhar and R. K. Rajaram

Bis(L-proline) hydrogen nitrate

Crystal data

2C5H9NO2·H+·NO3−

Mr = 293.28

Orthorhombic, P212121

a = 7.2006 (6) Å

b = 7.711 (1) Å

c = 24.060 (3) Å

V = 1335.9 (3) Å3

Z = 4

F(000) = 624

Dx = 1.458 Mg m−3

Dm = 1.454 Mg m−3

Dm measured by flotation method in a mixture

of carbon tetrachloride and xylene Mo Kα radiation, λ = 0.71073 Å Cell parameters from 25 reflections

θ = 11.3–13.9°

µ = 0.12 mm−1

T = 293 K Block, colourless 0.5 × 0.5 × 0.5 mm

Data collection

Enraf-Nonis CAD-4 diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

ω–2θ scans

Absorption correction: ψ scan (North et al., 1968)

Tmin = 0.916, Tmax = 0.937

3718 measured reflections

1430 independent reflections 1276 reflections with I > 2σ(I)

Rint = 0.019

θmax = 25.5°, θmin = 1.7°

h = −1→8

k = −1→9

l = −29→29

3 standard reflections every 60 min intensity decay: none

Refinement

Refinement on F2

Least-squares matrix: full

R[F2_{> 2}_σ₍_F2_{)] = 0.047}

wR(F2_{) = 0.121}

S = 1.16 1430 reflections 186 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H atoms treated by a mixture of independent and constrained refinement

w = 1/[σ2₍_F

o2) + (0.0703P)2 + 0.319P]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max < 0.001

Δρmax = 0.32 e Å−3

Δρmin = −0.29 e Å−3

Extinction correction: SHELXL97, Fc*_{=kFc[1+0.001xFc}2_λ3_/sin(2_θ_)]-1/4

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supporting information

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2_{against ALL reflections. The weighted}_R_-factor_wR_{and goodness of fit}_S_{are based on}_F2_,

conventional R-factors R are based on F, with F set to zero for negative F2_{. The threshold expression of}_F2_>_σ₍_F2_{) is used}

only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2

are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2₎

x y z Uiso*/Ueq

O1A 1.1931 (3) −0.0793 (3) 0.49046 (8) 0.0446 (6) O1B 1.0311 (3) 0.0038 (3) 0.41810 (8) 0.0450 (6) C11 1.0476 (4) −0.0425 (3) 0.46762 (11) 0.0316 (6) C12 0.8657 (4) −0.0524 (4) 0.49757 (10) 0.0324 (6)

H12 0.7794 −0.1230 0.4757 0.039*

N11 0.8923 (4) −0.1340 (3) 0.55183 (9) 0.0382 (6)

H11A 1.0057 −0.1088 0.5654 0.046*

H11B 0.8816 −0.2500 0.5490 0.046*

C13 0.7734 (5) 0.1195 (4) 0.51134 (13) 0.0468 (8)

H13A 0.8625 0.2029 0.5254 0.056*

H13B 0.7108 0.1679 0.4792 0.056*

C14 0.6374 (5) 0.0664 (5) 0.55541 (14) 0.0570 (9)

H14A 0.6004 0.1648 0.5780 0.068*

H14B 0.5275 0.0140 0.5392 0.068*

C15 0.7449 (5) −0.0629 (5) 0.58893 (12) 0.0493 (8)

H15A 0.8002 −0.0073 0.6211 0.059*

H15B 0.6639 −0.1552 0.6017 0.059*

O2A 0.5232 (3) −0.0304 (3) 0.40632 (9) 0.0511 (6) O2B 0.2852 (3) 0.0571 (5) 0.35494 (9) 0.0651 (8)

H2B 0.200 (8) 0.004 (7) 0.389 (2) 0.12 (2)*

C21 0.4573 (4) 0.0281 (4) 0.36512 (11) 0.0375 (7) C22 0.5786 (4) 0.0743 (4) 0.31718 (10) 0.0359 (7)

H22 0.5474 0.1910 0.3041 0.043*

N21 0.7797 (3) 0.0672 (4) 0.33214 (10) 0.0405 (6)

H21A 0.8234 0.1755 0.3370 0.049*

H21B 0.7941 0.0089 0.3643 0.049*

C23 0.5624 (5) −0.0517 (6) 0.26988 (13) 0.0549 (9)

H23A 0.4650 −0.0175 0.2443 0.066*

H23B 0.5373 −0.1681 0.2833 0.066*

C24 0.7500 (5) −0.0413 (8) 0.24289 (15) 0.0805 (15)

H24A 0.7755 −0.1464 0.2221 0.097*

H24B 0.7553 0.0565 0.2176 0.097*

C25 0.8848 (5) −0.0199 (6) 0.28760 (14) 0.0581 (10)

H25A 0.9887 0.0508 0.2756 0.070*

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supporting information

N 0.7577 (5) 0.4984 (4) 0.35805 (13) 0.0615 (9)

O1 0.6564 (5) 0.3986 (5) 0.38431 (13) 0.0893 (11) O2 0.8670 (4) 0.4309 (5) 0.32523 (12) 0.0804 (9) O3 0.7491 (9) 0.6519 (4) 0.36692 (17) 0.139 (2)

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

O1A 0.0324 (11) 0.0601 (12) 0.0411 (10) 0.0096 (11) 0.0011 (9) 0.0074 (10) O1B 0.0301 (10) 0.0690 (15) 0.0358 (10) 0.0006 (11) 0.0019 (9) 0.0107 (10) C11 0.0300 (14) 0.0301 (12) 0.0348 (12) −0.0012 (12) −0.0002 (11) 0.0001 (12) C12 0.0288 (14) 0.0364 (13) 0.0320 (12) 0.0000 (12) −0.0014 (11) 0.0033 (12) N11 0.0394 (14) 0.0413 (12) 0.0338 (11) 0.0011 (12) 0.0037 (10) 0.0041 (11) C13 0.0416 (18) 0.0450 (15) 0.0538 (17) 0.0093 (15) 0.0066 (16) 0.0067 (14) C14 0.0504 (19) 0.062 (2) 0.0592 (18) 0.012 (2) 0.0192 (17) −0.0004 (17) C15 0.0502 (18) 0.0605 (18) 0.0371 (14) −0.0017 (18) 0.0113 (14) −0.0027 (15) O2A 0.0397 (11) 0.0726 (15) 0.0409 (11) 0.0038 (13) 0.0020 (9) 0.0184 (12) O2B 0.0304 (11) 0.123 (2) 0.0424 (11) 0.0053 (16) 0.0035 (10) 0.0200 (14) C21 0.0327 (14) 0.0479 (16) 0.0320 (13) 0.0007 (14) −0.0001 (12) 0.0048 (13) C22 0.0287 (14) 0.0478 (16) 0.0311 (13) 0.0025 (13) −0.0024 (11) 0.0008 (12) N21 0.0317 (12) 0.0567 (14) 0.0332 (11) −0.0005 (13) −0.0024 (10) 0.0013 (12) C23 0.0444 (17) 0.079 (2) 0.0414 (15) −0.0037 (19) −0.0018 (14) −0.0174 (18) C24 0.049 (2) 0.145 (4) 0.0473 (17) 0.000 (3) 0.0097 (16) −0.032 (2) C25 0.0371 (16) 0.089 (3) 0.0479 (17) 0.005 (2) 0.0097 (14) −0.0088 (19) N 0.066 (2) 0.0639 (19) 0.0543 (16) 0.0107 (18) −0.0078 (16) −0.0059 (15) O1 0.088 (2) 0.095 (2) 0.085 (2) −0.018 (2) 0.0345 (19) −0.0282 (18) O2 0.0669 (18) 0.103 (2) 0.0715 (17) −0.0097 (19) 0.0269 (16) −0.0119 (17) O3 0.228 (6) 0.0598 (19) 0.129 (3) 0.027 (3) 0.019 (4) 0.006 (2)

Geometric parameters (Å, º)

O1A—C11 1.216 (3) O2B—H2B 1.11 (6)

O1B—C11 1.250 (3) C21—C22 1.490 (4)

C11—C12 1.497 (4) C22—N21 1.493 (4)

C12—N11 1.462 (3) C22—C23 1.501 (4)

C12—C13 1.519 (4) C22—H22 0.98

C12—H12 0.98 N21—C25 1.474 (4)

N11—C15 1.491 (4) N21—H21A 0.90

N11—H11A 0.90 N21—H21B 0.90

N11—H11B 0.90 C23—C24 1.501 (5)

C13—C14 1.500 (5) C23—H23A 0.97

C13—H13A 0.97 C23—H23B 0.97

C13—H13B 0.97 C24—C25 1.458 (5)

C14—C15 1.498 (5) C24—H24A 0.97

C14—H14A 0.97 C24—H24B 0.97

C14—H14B 0.97 C25—H25A 0.97

C15—H15A 0.97 C25—H25B 0.97

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supporting information

O2A—C21 1.188 (4) N—O1 1.234 (5)

O2B—C21 1.282 (4) N—O2 1.231 (4)

O1A—C11—O1B 125.4 (3) O2A—C21—C22 120.2 (3)

O1A—C11—C12 121.6 (2) O2B—C21—C22 112.1 (2)

O1B—C11—C12 113.0 (2) C21—C22—N21 111.9 (2)

N11—C12—C11 109.7 (2) C21—C22—C23 112.8 (3)

N11—C12—C13 103.8 (2) N21—C22—C23 103.6 (2)

C11—C12—C13 116.3 (2) C21—C22—H22 109.5

N11—C12—H12 108.9 N21—C22—H22 109.5

C11—C12—H12 108.9 C23—C22—H22 109.5

C13—C12—H12 108.9 C25—N21—C22 109.8 (2)

C12—N11—C15 106.4 (2) C25—N21—H21A 109.7

C12—N11—H11A 110.4 C22—N21—H21A 109.7

C15—N11—H11A 110.4 C25—N21—H21B 109.7

C12—N11—H11B 110.4 C22—N21—H21B 109.7

C15—N11—H11B 110.4 H21A—N21—H21B 108.2

H11A—N11—H11B 108.6 C22—C23—C24 102.9 (3)

C14—C13—C12 101.6 (2) C22—C23—H23A 111.2

C14—C13—H13A 111.4 C24—C23—H23A 111.2

C12—C13—H13A 111.4 C22—C23—H23B 111.2

C14—C13—H13B 111.4 C24—C23—H23B 111.2

C12—C13—H13B 111.4 H23A—C23—H23B 109.1

H13A—C13—H13B 109.3 C25—C24—C23 106.6 (3)

C15—C14—C13 103.0 (3) C25—C24—H24A 110.4

C15—C14—H14A 111.2 C23—C24—H24A 110.4

C13—C14—H14A 111.2 C25—C24—H24B 110.4

C15—C14—H14B 111.2 C23—C24—H24B 110.4

C13—C14—H14B 111.2 H24A—C24—H24B 108.6

H14A—C14—H14B 109.1 C24—C25—N21 104.3 (3)

N11—C15—C14 106.9 (2) C24—C25—H25A 110.9

N11—C15—H15A 110.3 N21—C25—H25A 110.9

C14—C15—H15A 110.3 C24—C25—H25B 110.9

N11—C15—H15B 110.3 N21—C25—H25B 110.9

C14—C15—H15B 110.3 H25A—C25—H25B 108.9

H15A—C15—H15B 108.6 O3—N—O1 119.4 (4)

C21—O2B—H2B 109 (3) O3—N—O2 124.2 (5)

O2A—C21—O2B 127.7 (3) O1—N—O2 116.3 (3)

O1A—C11—C12—N11 −8.3 (4) O2A—C21—C22—N21 −10.0 (5)

O1B—C11—C12—N11 170.7 (2) O2B—C21—C22—N21 170.9 (3)

O1A—C11—C12—C13 109.1 (3) O2A—C21—C22—C23 106.3 (3)

O1B—C11—C12—C13 −71.9 (3) O2B—C21—C22—C23 −72.8 (4)

C11—C12—N11—C15 151.9 (2) C21—C22—N21—C25 136.1 (3)

C13—C12—N11—C15 27.0 (3) C23—C22—N21—C25 14.3 (4)

N11—C12—C13—C14 −41.6 (3) C21—C22—C23—C24 −151.4 (3)

C11—C12—C13—C14 −162.2 (2) N21—C22—C23—C24 −30.2 (4)

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supporting information

C12—N11—C15—C14 −2.1 (3) C23—C24—C25—N21 −27.7 (5)

C13—C14—C15—N11 −23.9 (4) C22—N21—C25—C24 8.0 (5)

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

O2B—H2B···O1Bi _{1.11 (6)} _{1.40 (6)} _{2.414 (3)} _{148 (5)}

N11—H11A···O1ii _0.90 _2.30 _{3.045 (4)} ₁₄₁

N11—H11A···O3ii _0.90 _2.42 _{3.231 (6)} ₁₅₁

N11—H11B···O1Aiii _0.90 _2.12 _{2.825 (3)} ₁₃₅

N11—H11B···O2Aiv _0.90 _2.25 _{2.932 (3)} ₁₃₂

N21—H21B···O2A 0.90 2.22 2.676 (3) 111

N21—H21B···O1B 0.90 2.14 2.792 (3) 128

N21—H21A···O2 0.90 2.01 2.879 (5) 161

N21—H21A···O1 0.90 2.39 2.982 (4) 124